Synthesis, Table of Contents PAPER© Georg Thieme Verlag Stuttgart ˙ New YorkSynthesis of 1H-2-Benzopyran-5,8-dione Derivatives from 2-(1-Hydroxyalkyl)-1,4-benzoquinones and EnaminesKazuhiro Kobayashi*, Kosaku Nomura, Toshikazu Ogata, Miyuki Tanmatsu, Osamu Morikawa, Hisatoshi KonishiDepartment of Materials Science, Faculty of Engineering, Tottori University, Koyama-minami, Tottori 680-8552, JapanFax: +81(857)315263; e-Mail: kkoba@chem.tottori-u.ac.jp; Recommend Article Abstract Buy Article All articles of this category Abstract An efficient synthesis of the title benzopyranodione derivatives based on a Michael addition/cyclization sequence between 2-(1-hydroxyalkyl)-1,4-benzoquinones and enamines (or an imine) is described. Key words enamines - heterocycles - benzoquinones Full Text References References <A NAME="RF09702SS-1A">1a</A> Kobayashi K. Uchida M. Uneda T. Tanmatsu M. Morikawa O. Konishi H. Tetrahedron Lett. 1998, 39: 7725 <A NAME="RF09702SS-1B">1b</A> Kobayashi K. Uchida M. Uneda T. Yoneda K. Tanmatsu M. Morikawa O. Konishi H. J. Chem. Soc., Perkin Trans 1 2001, 2977 <A NAME="RF09702SS-2A">2a</A> Kobayashi K. Uneda T. Kawakita M. Morikawa O. Konishi H. Tetrahedron Lett. 1997, 38: 837 <A NAME="RF09702SS-2B">2b</A> Kobayashi K. Tanaka K. Uneda T. Maeda M. Morikawa O. Konishi H. Synthesis 1998, 1243 <A NAME="RF09702SS-2C">2c</A> Kobayashi K. Taki T. Kawakita M. Uchida M. Morikawa O. Konishi H. Heterocycles 1999, 51: 349 <A NAME="RF09702SS-2D">2d</A> Kobayashi K. Furuta Y. Matsuoka H. Uchida M. Morikawa O. Konishi H. Chem. Lett. 1999, 503 <A NAME="RF09702SS-2E">2e</A> Kobayashi K. Takanohashi A. Watanabe S. Morikawa O. Konishi H. Tetrahedron Lett. 2000, 41: 7657 <A NAME="RF09702SS-2F">2f</A> Tanaka K. Takanohashi A. Morikawa O. Konishi H. Kobayashi K. Heterocycles 2001, 55: 1561 <A NAME="RF09702SS-2G">2g</A> Kobayashi K. Yoneda K. Uchida M. Matsuoka H. Morikawa O. Konishi H. Heterocycles 2001, 55: 2423 <A NAME="RF09702SS-3">3</A> Garner P. Anderson JT. Turske RA. Chem. Commun. 2000, 1579 <A NAME="RF09702SS-4">4</A> Stevens RV. Vinogradoff AP. J. Org. Chem. 1985, 50: 4056 For previous syntheses, see: <A NAME="RF09702SS-5A">5a</A> Retamal JI. Ruiz VN. Tapia RA. Valderrama JA. Vega JC. Synth. Commun. 1982, 12: 279 <A NAME="RF09702SS-5B">5b</A> Giles RGF. Green IR. Pestatna JAX. J. Chem. Soc., Perkin Trans. 1 1984, 2389 <A NAME="RF09702SS-5C">5c</A> Green IR. Hugo VI. Oosthuisen FJ. van Eeden N. Giles RGF. S. Afr. J. Chem. 1995, 48: 15 ; Chem. Abstr. 1996, 124 , 260773e <A NAME="RF09702SS-5D">5d</A> Esterhuyse AJ. Hugo VI. Pestatna JAX. Snijman PW. Green IR. S. Afr. J. Chem. 1993, 46: 34 ; Chem. Abstr. 1994, 120, 244537t <A NAME="RF09702SS-5E">5e</A> Xiong Y. Xia H. Moore HW. J. Org. Chem. 1995, 60: 6460 <A NAME="RF09702SS-5F">5f</A> de Koning CB. Green IR. Michael JP. Oliveira JR. Tetrahedron Lett. 1997, 38: 5055 <A NAME="RF09702SS-5G">5g</A> Green IR. de Koning CB. Hugo VI. S. Afr. J. Chem. 1999, 52: 112 ; Chem. Abstr. 2000, 132 , 264944r <A NAME="RF09702SS-5H">5h</A> Giles RGF. Joll CA. J. Chem. Soc., Perkin Trans. 1 1999, 3039 <A NAME="RF09702SS-5I">5i</A> Valderrama JA. Pessoa-Mahama D. Tapia RA. de Arias AR. Nakayama H. Torres S. Miret J. Ferreira ME. Tetrahedron 2001, 57: 8653 <A NAME="RF09702SS-6A">6a</A> Kometani T. J. Chem. Soc., Perkin Trans. 1 1981, 1191 <A NAME="RF09702SS-6B">6b</A> Attardo G, Xu YC, Lavallée JF, Rej R, and Belleau B. inventors; PCT Int. Patent 19725. ; Chem. Abstr. 1992, 117, 27052q <A NAME="RF09702SS-6C">6c</A> Lavallée JF. Rej R. Courchesne M. Nguyen D. Attardo G. Tetrahedron Lett. 1993, 34: 3519 <A NAME="RF09702SS-6D">6d</A> Xu YC. Lebeau E. Attardo G. Mters PL. Gillard JW. J. Org. Chem. 1994, 59: 4868 <A NAME="RF09702SS-6E">6e</A> Attardo G, Breining T, Courchesne M, Kraus JL, Lamothe S, Lavallée JF, Lebeau E, Nguyen D, and Rej R. inventors; PCT Int. Patent 11382. ; Chem. Abstr. 1996, 124, 30252e <A NAME="RF09702SS-6F">6f</A> Toedter C. Lackner H. Liebigs Ann. Chem. 1996, 1385 <A NAME="RF09702SS-6G">6g</A> Attardo G, Kraus JL, Courchesne M, Lamothe S, Lavallée JF, Lebeau E, Nguyen D, Rej R, St-Denis Y, Wang W, Xu YC, Barbeau F, and Belleau B. inventors; US Patent 5593970. ; Chem. Abstr. 1997, 126; 199791g <A NAME="RF09702SS-6H">6h</A> Donner CD. Gill M. Tetrahedron Lett. 1999, 40: 3921 <A NAME="RF09702SS-6I">6i</A> Giles RGF. Green IR. Oosthuizen FJ. Taylor CP. Tetrahedron Lett. 2001, 42: 5753 <A NAME="RF09702SS-7">7</A> The reaction in toluene proceeded sluggishly and gave a lower yield of the expected product. <A NAME="RF09702SS-8">8</A> Stork G. Brizzolara A. Landesman H. Szmuszkovicz J. Terrell R. J. Am. Chem. Soc. 1963, 85: 207 <A NAME="RF09702SS-9">9</A> Bunnelle WH. Singam PR. Narayanan BA. Bradshaw CW. Liou TS. Synthesis 1997, 439 <A NAME="RF09702SS-10">10</A> Kessar SV. Gupta YP. Mohammad T. Goyal M. Sawal KK. J. Chem. Soc., Chem. Commun. 1983, 400 <A NAME="RF09702SS-11">11</A> Cason J. Org. React. 1948, 4: 305